CA1305271C - Photochromic articles - Google Patents

Photochromic articles

Info

Publication number: CA1305271C
Authority: CA; Canada
Prior art keywords: photochromic; oxazine; article according; spiro; compound
Prior art date: 1986-05-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000536229A

Other languages

English (en)

French (fr)

Inventor

Martin Rickwood

John David Hepworth

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pilkington Group Ltd

Original Assignee

Pilkington PLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-05-01

Filing date

1987-05-01

Publication date

1992-07-14

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10597204&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1305271(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1987-05-01 Application filed by Pilkington PLC filed Critical Pilkington PLC

1992-07-14 Application granted granted Critical

1992-07-14 Publication of CA1305271C publication Critical patent/CA1305271C/en

2009-07-14 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

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230000008859 change Effects 0.000 claims abstract description 4
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BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 28
-1 tri-substituted phenyl Chemical group 0.000 claims description 27
239000000178 monomer Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 13
150000001412 amines Chemical group 0.000 claims description 11
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125000001424 substituent group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 7
125000001072 heteroaryl group Chemical group 0.000 claims description 7
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125000002723 alicyclic group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
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125000005842 heteroatom Chemical group 0.000 claims description 4
229920005862 polyol Polymers 0.000 claims description 4
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125000003003 spiro group Chemical group 0.000 claims description 4
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
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HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
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125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 2
229920002301 cellulose acetate Polymers 0.000 claims description 2
229920006217 cellulose acetate butyrate Polymers 0.000 claims description 2
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
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QYJHIFFEJFVRBZ-UHFFFAOYSA-N 1',3',3'-trimethyl-6-(4-methylpiperazin-1-yl)spiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound CN1C2=CC=CC=C2C(C)(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCN(C)CC1 QYJHIFFEJFVRBZ-UHFFFAOYSA-N 0.000 claims 1
VBGVMVBBKHCPIQ-UHFFFAOYSA-N 1',3',3'-trimethyl-6-morpholin-4-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound CN1C2=CC=CC=C2C(C)(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCOCC1 VBGVMVBBKHCPIQ-UHFFFAOYSA-N 0.000 claims 1
YAWJWXXKKHOMQT-UHFFFAOYSA-N 1',3',3'-trimethyl-6-piperidin-1-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound CN1C2=CC=CC=C2C(C)(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCCCC1 YAWJWXXKKHOMQT-UHFFFAOYSA-N 0.000 claims 1
ITKWLWLLMYQCBK-UHFFFAOYSA-N 1',3',3'-trimethyl-6-piperidin-1-ylspiro[benzo[f][1,4]benzoxazine-3,2'-pyrrolo[2,3-b]pyridine] Chemical compound CN1C2=NC=CC=C2C(C)(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCCCC1 ITKWLWLLMYQCBK-UHFFFAOYSA-N 0.000 claims 1
ANLXBOYEDMKYKK-UHFFFAOYSA-N 1',3',3'-trimethyl-6-thiomorpholin-4-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound CN1C2=CC=CC=C2C(C)(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCSCC1 ANLXBOYEDMKYKK-UHFFFAOYSA-N 0.000 claims 1
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DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 1
VYIUIBDVKHQJNA-UHFFFAOYSA-N 5'-methoxy-1',3',3'-trimethyl-6-morpholin-4-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound CC1(C)C2=CC(OC)=CC=C2N(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCOCC1 VYIUIBDVKHQJNA-UHFFFAOYSA-N 0.000 claims 1
CNJRLXXIXOGBQA-UHFFFAOYSA-N 5'-methoxy-1',3',3'-trimethyl-6-piperidin-1-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound CC1(C)C2=CC(OC)=CC=C2N(C)C1(C=NC1=C2C=CC=CC2=2)OC1=CC=2N1CCCCC1 CNJRLXXIXOGBQA-UHFFFAOYSA-N 0.000 claims 1
BOOLRCVSKFTZPK-UHFFFAOYSA-N 9-methoxy-1',3',3'-trimethyl-6-morpholin-4-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound C=1C=2OC3(C(C4=CC=CC=C4N3C)(C)C)C=NC=2C2=CC(OC)=CC=C2C=1N1CCOCC1 BOOLRCVSKFTZPK-UHFFFAOYSA-N 0.000 claims 1
XMMMOVQTCUDSQW-UHFFFAOYSA-N 9-methoxy-1',3',3'-trimethyl-6-piperidin-1-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound C=1C=2OC3(C(C4=CC=CC=C4N3C)(C)C)C=NC=2C2=CC(OC)=CC=C2C=1N1CCCCC1 XMMMOVQTCUDSQW-UHFFFAOYSA-N 0.000 claims 1
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AQCQTMCGRKQYSO-UHFFFAOYSA-N n,n,1',3',3'-pentamethylspiro[2,4-dihydro-1,4-benzoxazine-3,2'-indole]-6-amine Chemical compound CN1C2=CC=CC=C2C(C)(C)C11COC2=CC=C(N(C)C)C=C2N1 AQCQTMCGRKQYSO-UHFFFAOYSA-N 0.000 claims 1
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JXHMIEYQSFUORQ-UHFFFAOYSA-N n,n-diethyl-1',3',3'-trimethylspiro[2,4-dihydro-1,4-benzoxazine-3,2'-indole]-6-amine Chemical compound CN1C2=CC=CC=C2C(C)(C)C11COC2=CC=C(N(CC)CC)C=C2N1 JXHMIEYQSFUORQ-UHFFFAOYSA-N 0.000 claims 1
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238000005213 imbibition Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
239000003999 initiator Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
125000005641 methacryl group Chemical group 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
150000002791 naphthoquinones Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000005634 peroxydicarbonate group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000004088 simulation Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
IAHPADQGUAKOQZ-UHFFFAOYSA-N spiro[1,3-dihydroindole-2,3'-benzo[f][1,4]benzoxazine] Chemical compound C1=CC=CC2=C(N=CC3(NC4=CC=CC=C4C3)O3)C3=CC=C21 IAHPADQGUAKOQZ-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Eyeglasses (AREA)
Compositions Of Macromolecular Compounds (AREA)
Materials For Medical Uses (AREA)

CA000536229A 1986-05-01 1987-05-01 Photochromic articles Expired - Lifetime CA1305271C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8,610,709		1986-05-01
GB868610709A GB8610709D0 (en)	1986-05-01	1986-05-01	Photochromic lenses

Publications (1)

Publication Number	Publication Date
CA1305271C true CA1305271C (en)	1992-07-14

Family

ID=10597204

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000536229A Expired - Lifetime CA1305271C (en)	1986-05-01	1987-05-01	Photochromic articles

Country Status (15)

Country	Link
US (1)	US4913544A (de)
EP (1)	EP0245020B1 (de)
JP (1)	JP2690305B2 (de)
KR (1)	KR940007779B1 (de)
AR (1)	AR246355A1 (de)
AT (1)	ATE68053T1 (de)
AU (1)	AU605763B2 (de)
BR (1)	BR8702162A (de)
CA (1)	CA1305271C (de)
DE (1)	DE3773426D1 (de)
ES (1)	ES2027292T3 (de)
FI (1)	FI90560C (de)
GB (1)	GB8610709D0 (de)
GR (1)	GR3003252T3 (de)
ZA (1)	ZA873011B (de)

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1986
- 1986-05-01 GB GB868610709A patent/GB8610709D0/en active Pending
1987
- 1987-04-24 AU AU71966/87A patent/AU605763B2/en not_active Expired
- 1987-04-27 ZA ZA873011A patent/ZA873011B/xx unknown
- 1987-04-27 FI FI871826A patent/FI90560C/fi not_active IP Right Cessation
- 1987-04-29 AT AT87303819T patent/ATE68053T1/de not_active IP Right Cessation
- 1987-04-29 DE DE8787303819T patent/DE3773426D1/de not_active Expired - Lifetime
- 1987-04-29 EP EP87303819A patent/EP0245020B1/de not_active Expired - Lifetime
- 1987-04-29 ES ES198787303819T patent/ES2027292T3/es not_active Expired - Lifetime
- 1987-04-30 KR KR1019870004209A patent/KR940007779B1/ko not_active IP Right Cessation
- 1987-04-30 JP JP62104851A patent/JP2690305B2/ja not_active Expired - Lifetime
- 1987-04-30 AR AR87307432A patent/AR246355A1/es active
- 1987-04-30 BR BR8702162A patent/BR8702162A/pt not_active IP Right Cessation
- 1987-05-01 US US07/044,715 patent/US4913544A/en not_active Expired - Lifetime
- 1987-05-01 CA CA000536229A patent/CA1305271C/en not_active Expired - Lifetime
1991
- 1991-12-02 GR GR91401880T patent/GR3003252T3/el unknown

Also Published As

Publication number	Publication date
ZA873011B (en)	1988-02-24
GR3003252T3 (en)	1993-02-17
ES2027292T3 (es)	1992-06-01
AU605763B2 (en)	1991-01-24
DE3773426D1 (de)	1991-11-07
ATE68053T1 (de)	1991-10-15
KR870011492A (ko)	1987-12-23
US4913544A (en)	1990-04-03
JPS62288830A (ja)	1987-12-15
FI871826A0 (fi)	1987-04-27
BR8702162A (pt)	1988-02-09
AU7196687A (en)	1987-11-05
FI90560B (fi)	1993-11-15
EP0245020A3 (en)	1988-08-03
EP0245020A2 (de)	1987-11-11
GB8610709D0 (en)	1986-06-04
FI90560C (fi)	1994-02-25
AR246355A1 (es)	1994-07-29
JP2690305B2 (ja)	1997-12-10
EP0245020B1 (de)	1991-10-02
KR940007779B1 (ko)	1994-08-25
FI871826A (fi)	1987-11-02

Publication	Publication Date	Title
CA1305271C (en)	1992-07-14	Photochromic articles
US4816584A (en)	1989-03-28	Photochromic spiro(indoline)benzoxazines
US4968454A (en)	1990-11-06	Variable-light transmittance article and method for preparing same
EP1112263B1 (de)	2005-06-08	Polymerisierbare polyalkoxylierte naphthopyrane
US4980089A (en)	1990-12-25	Photochromic spiropyran compounds
US4931221A (en)	1990-06-05	Photochromic spiropyran compounds
EP0560898A4 (en)	1993-11-18	Photochromic naphthopyrans
WO2000002883A2 (en)	2000-01-20	Photochromic six-membered heterocyclic-fused naphthopyrans
US4986934A (en)	1991-01-22	Photochromic compound and articles containing the same
US5021196A (en)	1991-06-04	Method for preparing variable-light transmittance article
EP1025108B1 (de)	2002-07-24	Photochrome spiro(indolin) fluoranthenoxazine verbindungen
WO1989011482A1 (en)	1989-11-30	Photochromic compound and articles containing the same
JPH07242672A (ja)	1995-09-19	新規スピロオキサジン類およびその眼科光学分野での使用方法
US4909963A (en)	1990-03-20	Photochromic article
EP0785936A4 (de)	1998-07-08	Photochrome naphthoxazin-verbindungen
CA1288767C (en)	1991-09-10	Photochromic compound and articles containing the same
GB2190088A (en)	1987-11-11	Photochromic articles
EP1000025B1 (de)	2007-02-21	Substituierte naphthopyrane
MXPA01002556A (en)	2002-03-05	Polymerizable polyalkoxylated naphthopyrans
MXPA01002555A (en)	2002-05-09	Polyalkoxylated naphthopyrans

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